Fly So Free electrified the racing world in 1990 with a strong two year old campaign, capped by a commanding victory in the Breeders' Cup Juvenile. Trained by Flint “Scotty” Schulhofer, and ridden by Jose Santos, Fly So Free's victory secured the two year old championship. The promising colt was owned by Broadway producer Tommy Valando.
For Schulhofer, it was his first Breeders' cup victory, and a race that launched him to the elite level of Thoroughbred racing. He would later be elected to the Hall of Fame. Fly So Free carried his Breeders' Cup Juvenile success into this three year old year, winning the Grade 1 Florida Derby, but finishing a disappointing fifth in the Kentucky Derby. He would run in two more Breeders' Cup races, finishing fourth in the 1991 Classic, and ninth in the 1993 Sprint.